I liked the book until the end. I don't care for sad ending and didn't realize it was going to be.
It was more clear in the book, that he was intrinsically tied to Clare. So he kept traveling to where ever she was. He kept returning to the meadow because that was her home.
Even in the movie she said, "She never had a choice about being with him & loving him." In the same way, neither did he. Except he could have waited till she was older to consummate their love.
As for him ending up naked, he couldn't take anything with him when he time traveled. Only
he traveled, no material objects. It isn't like the
Star Trek transporter, where a person and whatever he has with him materializes & dematerializes. Only Henry traveled.